Winston-Salem holiday lettings

We found 529 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Winston-Salem by choosing from 182 houses, 105 apartments and other holiday rentals. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winston-Salem

Showing deals for:3 Oct - 10 Oct
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Why visit Winston-Salem

  • Cultural richness: Explore a variety of art museums and historic villages that showcase Winston-Salem's vibrant heritage.
  • Charming neighbourhoods: Discover delightful areas like Karmel Hill, perfect for leisurely strolls and local experiences.
  • Family-friendly activities: Enjoy numerous attractions that cater to all ages, ensuring fun for the entire family.
  • Diverse accommodation options: Choose from quaint private holiday homes, cosy apartments, and charming cabins for a memorable stay.
  • Outdoor adventures: Take advantage of the beautiful surroundings with opportunities for hiking and exploration.

Popular types of accommodation in Winston-Salem

Planning a getaway to Winston-Salem? The next exciting step is selecting your accommodation. Discover a variety of options, including charming houses, cosy apartments, and delightful cabins. With numerous rental listings and properties available, you can easily find the perfect home for rent to suit your needs. Explore the vibrant offerings of Winston-Salem rentals and make your stay truly memorable.

  • Houses: The most sought-after option in Winston-Salem, offering ample space and privacy for families or groups.
  • Apartments: A popular choice for those seeking a convenient and modern base to explore the city.
  • Cabins: Ideal for nature enthusiasts, these rentals provide a serene escape in a rustic setting.
  • Cottages: Charming and quaint, perfect for a romantic getaway or a tranquil retreat.
  • Condos: A stylish option that combines comfort with access to amenities.**

Top attractions in Winston-Salem

Winston-Salem is an ideal destination for city-themed, family, and outdoor holidays. Visitors can explore a range of attractions, including modern colleges, historic villages, and art museums, offering enriching cultural experiences. Whether you're seeking family fun or an immersive city experience, Winston-Salem has something to delight every traveller.

  • Wake Forest University: A prestigious modern university, Wake Forest boasts a beautiful campus with a blend of traditional and contemporary architecture. Its vibrant atmosphere is perfect for exploring art galleries, libraries, and lush green spaces.
  • Benton Convention Center: This dynamic event venue is ideal for conferences and exhibitions. Its modern facilities and business-centric vibe make it a hub for professionals and visitors alike, hosting a variety of events throughout the year.
  • Old Salem: A charming historic village, Old Salem offers a glimpse into the Moravian community's past. Wander through restored buildings, enjoy traditional crafts, and savour authentic cuisine in a picturesque setting that reflects rich cultural heritage.

Things to do recommended for couples

For a delightful couple's getaway in Winston-Salem, explore the enchanting Weathervane Winery, only 8.1km away, or visit the charming Junius Lindsay Vineyard, situated 7.5km from the city. Don't miss Medaloni Cellars and Vineyards, a romantic escape just 8.7km away, perfect for wine lovers.

Things to do recommended for families

Families visiting Winston-Salem can enjoy the energetic atmosphere at Lawrence Joel Veterans Memorial Coliseum and Truist Stadium, perfect for sports enthusiasts. For a day of adventure, head to Airbound Trampoline Park, where kids can bounce around and have great fun together.

Things to do recommended for groups

Groups visiting Winston-Salem can indulge in shopping at Hanes Mall, enjoy thrilling races at Bowman Gray Stadium, and catch a film at Grand 18-Winston-Salem, making for a delightful blend of shopping, sports, and entertainment suitable for all ages.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, opting for a longer stay often results in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay in and around Winston-Salem

Winston-Salem, North Carolina, offers a delightful blend of family-friendly activities and vibrant city life. Visitors can explore charming neighbourhoods like Karmel Hill, indulge in local excursions, and enjoy the warm atmosphere created by friendly locals. Whether you're seeking outdoor adventures or a cultural experience, Winston-Salem and its surrounding areas promise a memorable holiday filled with diverse vibes and exciting discoveries.

  • Winston-Salem: Winston-Salem is a vibrant city known for its rich history and modern charm. Nestled in the heart of North Carolina, it offers a delightful blend of family-friendly activities and business opportunities. Visitors can explore the local shopping centres, enjoy educational institutions, and relax by the scenic lake. The city is home to notable landmarks such as a prestigious modern college university and a lively stadium, making it an excellent destination for both leisure and work.
  • Kernersville: Located approximately 6.2km from Winston-Salem, Kernersville is a picturesque city perfect for those seeking outdoor adventures and scenic beauty. This charming area is ideal for families, offering a variety of activities, including visits to local educational facilities and an arena entertainment complex. Nature enthusiasts will appreciate the lovely lakes and expansive parks, while the proximity to a modern college university and stadium adds to its appeal as a well-rounded destination.
  • Wallburg: Wallburg is a quaint village that provides a romantic and scenic experience for visitors. Situated near Winston-Salem, this lovely area is perfect for couples and families alike, with plenty of outdoor activities to enjoy. Golf enthusiasts can take advantage of the local golf courses, while the nearby lake and educational facilities add a touch of charm. With its serene atmosphere and beautiful surroundings, Wallburg is a delightful retreat for those looking to unwind and connect with nature.

Best time to go to Winston-Salem

If you're planning a trip to Winston-Salem, it's a good idea to check both the weather and property rates. The warmest months are July and July. Peak season runs in April, April, July, July, September and September, while off-peak times, like January, November, November to December and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly Low
January38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly Low
February42.4°F (5.8°C)Light RainMostly SunnyAverageSlightly Low
February42.4°F (5.8°C)Light RainMostly SunnyAverageSlightly Low
March49.1°F (9.5°C)Light RainMostly SunnyAverageSlightly Low
March49.1°F (9.5°C)Light RainMostly SunnyAverageSlightly Low
April58.3°F (14.6°C)Light RainMostly SunnySlightly HighSlightly High
April58.3°F (14.6°C)Light RainMostly SunnySlightly HighSlightly High
May67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
May67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
June75.0°F (23.9°C)Light RainMostly SunnyAverageAverage
June75.0°F (23.9°C)Light RainMostly SunnyAverageAverage
July78.8°F (26.0°C)Light RainMostly SunnySlightly HighAverage
July78.8°F (26.0°C)Light RainMostly SunnySlightly HighAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
September71.1°F (21.7°C)Light RainMostly SunnySlightly HighAverage
September71.1°F (21.7°C)Light RainMostly SunnySlightly HighAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
December43.0°F (6.1°C)Light RainMostly SunnySlightly LowAverage
December43.0°F (6.1°C)Light RainMostly SunnySlightly LowAverage

What do I need to keep in mind when booking a vacation in 'Winston-Salem

If you're travelling with a group, as a family, with pets, or seeking extended stays, it's important to use the appropriate filters to prioritise your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winston-Salem with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor area for group gatherings. Luckily, you can easily apply filters for these options and many more on Vrbo.
  • Traveling to Winston-Salem with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Winston-Salem: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winston-Salem: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. It may also be beneficial to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume from where you last stopped, or review and arrange your travel plans. You'll discover your saved or booked properties neatly organised into categories such as Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The lush setting of Winston-Salem is ready to explore

The area's art galleries and museums are just some of the reasons to come on holiday to Winston-Salem. Renowned for its sporting events, shopping and forests, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winston-Salem

Are you hoping to discover attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Winston-Salem a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Salem Glen Golf & Country Club (11.7 mi / 18.8 km)
  • Divine Llama Vineyards (15.1 mi / 24.4 km)
  • Richard Childress Vineyards (17.9 mi / 28.9 km)
  • Farmington Dragway (18.8 mi / 30.2 km)
  • The Candy Factory (19 mi / 30.6 km)
  • Celebration Station (19.8 mi / 31.9 km)

Exploring the natural landscape of Winston-Salem

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winston-Salem is a great place to spend some time outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Reynolda Gardens (2.9 mi / 4.6 km)
  • Paul J Ciener Botanical Garden (9.5 mi / 15.3 km)
  • Tanglewood Park (11.4 mi / 18.4 km)
  • Truist Sports Park (11.5 mi / 18.6 km)
  • BB&T Soccer Park (11.6 mi / 18.7 km)
  • Belews Lake Park (14.4 mi / 23.2 km)

Transport to and around Winston-Salem

Fly into Winston-Salem, NC (INT-Smith Reynolds), the closest airport, located 2.7 mi (4.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Greensboro, NC (GSO-Piedmont Triad Intl.), which is 17.1 mi (27.6 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Winston-Salem?
Apartments are the most popular kind of holiday rental in Winston-Salem, according to our data. Even if you have a different vision in mind, Vrbo has properties in all shapes and sizes. Browse our options to find your ideal match.
How much does it cost to rent a holiday rental in Winston-Salem?
Length of stay, season and property type are some things that can affect the price of a holiday home. Simply enter your travel dates to find your dream escape. From comfy cottages to plush villas, all Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Winston-Salem?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Winston-Salem travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to choose the features and amenities you want in your beach house.
Are there pet-friendly holiday rentals in Winston-Salem?
Pack a suitcase for the pup in your life because Winston-Salem has 12 properties that put out the welcome mat to pets. Let your four-legged buddy have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
What are popular rental amenities in Winston-Salem?
Some of the most popular rental amenities people look for in Winston-Salem are nearby museums, a swimming pool and a barbecue grill. Whether you're on a trip with pals, family or even pets, Vrbo holiday homes come with the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday rentals in Winston-Salem?
Take your pick of three Vrbo holiday rentals in Winston-Salem that can accommodate five or more guests. You'll enjoy all the room and privacy you need to spend time with your nearest and dearest --- and nobody else.
Are there holiday rentals in Winston-Salem that welcome kids?
Gather your whole family for an unforgettable adventure in Winston-Salem at one of our 12 family-friendly holiday homes. A lot of these stays provide amenities that are just perfect for getaways with youngsters, such as full kitchens, extra bedrooms and private pools. Just click on the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Winston-Salem?
Keep the kids amused at these awesome family-friendly attractions in Winston-Salem:

  • Airbound Trampoline Park
  • SciWorks
  • Old Salem

Are there one-bedroom holiday rentals in Winston-Salem?
Yes, there are four one-bedroom properties in Winston-Salem to select from. A one-bedroom holiday rental is a superb choice if it's just you and your sweetheart or if you're travelling on your own. Add in more space, privacy and convenience compared to a regular hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom holiday rentals in Winston-Salem?
Gather your loved ones and enjoy a relaxing escape in one of the three two-bedroom holiday properties Winston-Salem has to offer.
Are there holiday rentals with WiFi in Winston-Salem?
Winston-Salem has three holiday rentals with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to updating your social media, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Winston-Salem?
Work out your travel dates and then use our filter tool to search for holiday rentals with ac in Winston-Salem on Vrbo. With 12 air-conditioned properties available, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Winston-Salem?
The age limit can vary across properties on Vrbo, so look at the rules of the holiday home in Winston-Salem you want. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Winston-Salem for?
It's really down to the Winston-Salem property. To view a list of options offering extended stays, simply type your dates and number of people into the Vrbo search page. Look forward to having the whole property to yourself, along with home comforts like a full kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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